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Visible-light mediated oxidative ring expansion of anellated cyclopropanes to fused endoperoxides with antimalarial activity

Budde, Simon ; Goerdeler, Felix ; Floß, Johannes ; Kreitmeier, Peter ; Hicks, Elliot F. ; Moscovitz, Oren ; Seeberger, Peter H. ; Davies, Huw M. L. ; Reiser, Oliver



Abstract

A visible light mediated ring expansion of readily available carbo- and heterocyclic anellated cyclopropanes by molecular oxygen at ambient pressure has been developed. Tolerating a variety of functional groups, the reaction yields fused 1,2-dioxolanes, which were tested for antimalarial activity given their close analogy to the active principle of approved drugs such as artemisinin.


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